One of the driving forces in the Boro engine room, Bailey has played his part in helping the club emerge as Championship promotion contenders this season.
But away from the frantic play-off battle, Boro also have the chance to book a place in the League Cup last four - a competition they have fond memories of, being the only major trophy they have ever won back in 2004.
Boro fans who face the midweek trip to Wales, have been boosted by the news that sponsors Capital One have agreed to pay for the visiting fans in recognition of their commitment to the tournament having been drawn away from home a remarkable 12 times in succession, dating back to 2008.
"It is great the fans are getting something back, they have been behind us all season and for them to get some reward this excellent," Bailey told Sky Sports.
"It is a long way for the fans to go but hopefully we can send them home with a smile on their faces."
Boro travel to South Wales sitting in third place, but they face a Swansea side who have impressed in the Premier League this season.
"They are clearly a good side, they have had some great results and against some of the best teams in the Premier League," Bailey continued.
"We know they will go into the game as favourites, but we have our own qualities and know we are capable of giving them a game.
"Promotion remains our aim, and I am sure the fans want us to win promotion above all - but a cup run is always good thing and for us to get to this stage has provided us with a boost."